ChemSpider 2D Image | Itraconazole | C35H38Cl2N8O4

Itraconazole

  • Molecular FormulaC35H38Cl2N8O4
  • Average mass705.633 Da
  • Monoisotopic mass704.239319 Da
  • ChemSpider ID49927
  • defined stereocentres - 2 of 3 defined stereocentres


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(±)-1-sec-Butyl-4-[p-[4-[p-[[(2R*,4S*)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-d2-1,2,4-triazolin-5-one
2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
2-(Butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorphenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-on
2-sec-Butyl-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one [ACD/IUPAC Name]
2-sec-Butyl-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophényl)-2-(1H-1,2,4-triazol-1-ylméthyl)-1,3-dioxolan-4-yl]méthoxy}phényl)-1-pipérazinyl]phényl}-2,4-dihydro-3H-1,2,4-triazol-3-one [French] [ACD/IUPAC Name]
2-sec-Butyl-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one
2-sec-Butyl-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorphenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-1-piperazinyl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-on [German] [ACD/IUPAC Name]
3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)- [ACD/Index Name]
4-(4-{4-[4-({[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl}oxy)phenyl]piperazin-1-yl}phenyl)-2-(1-methylpropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2-(1-methylpropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

R 51211 [DBID]
AIDS007334 [DBID]
AIDS-007334 [DBID]
AIDS093050 [DBID]
AIDS-093050 [DBID]
AIDS121432 [DBID]
AIDS-121432 [DBID]
BRN 6042047 [DBID]
CHEBI:6076 [DBID]
D00350 [DBID]
More...
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      solid Oxford University Chemical Safety Data (No longer updated) More details
    • Stability:

      Stable. Incompatible with strong oxidizing agents. Oxford University Chemical Safety Data (No longer updated) More details
    • Toxicity:

      ORL-RAT LD50 > 320 mg kg-1, IVN-RAT LD50 40 mg kg-1, ORL-MUS LD50 > 320 mg kg-1, ORL-DOG LD50 > 200 mg kg-1, ORL-GPG LD50 > 160 mg kg-1 Oxford University Chemical Safety Data (No longer updated) More details
    • Safety:

      J02AC02 Wikidata Q411229
      Minimize exposure. Oxford University Chemical Safety Data (No longer updated) More details
    • Target Organs:

      Antibiotic TargetMol T1011
    • Chemical Class:

      An <element>N</element>-arylpiperazine that is <stereo>cis</stereo>-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a <ital>p</ital>-[(<plusmn/>)1-<ital>sec</ital>-butyl-5-oxo-1,5-dihydro-4<element>H</element>-1,2,4-triazol-4-yl]phenyl group. A potent P-glycoprotein and CYP3A4 inhi bitor, it is used as an antifungal drug for the treatment of various fungal infections, including aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, hi stoplasmosis, and sporotrichosis. ChEBI CHEBI:6076
    • Drug Status:

      approved BIONET-Key Organics KS-1268
    • Bio Activity:

      14-?? Demethylase TargetMol T1011
      7-TM Receptors Tocris Bioscience 5981
      Antifungal MedChem Express HY-17514
      Anti-infection MedChem Express HY-17514
      Anti-infection; MedChem Express HY-17514
      Itraconazole is a triazole antifungal agent. MedChem Express
      Itraconazole is a triazole antifungal agent.; IC50 Value: N/A; Target: antifungal; in vitro: Itraconazole is pharmacologically distinct from other azole antifungal agents in that it is the only inhibitor in this class that has been shown to inhibit both the hedgehog signaling pathway and angiogenesis[1, 2]. MedChem Express HY-17514
      Itraconazole is a triazole antifungal agent.;IC50 Value: N/A;Target: antifungal;In vitro: Itraconazole is pharmacologically distinct from other azole antifungal agents in that it is the only inhibitor in this class that has been shown to inhibit both the hedgehog signaling pathway and angiogenesis[1, 2]. These distinct activities are unrelated to inhibition of the cytochrome P450 lanosterol 14 alpha-demethylase and the exact molecular targets responsible remain unidentified. Functionally, the antiangiogenic activity of itraconazole has been shown to be linked to inhibition of glycosylation, VEGFR2 phosphorylation and cholesterol biosynthesis pathways [2].Evidence suggests the structural determinants for inhibition of hedgehog signaling by itraconazole are recognizably different from those associated with antiangiogenic activity [3].;In vivo: Nine volunteers were given either 200 mg itraconazole, or matched placebo orally once daily for 4 days. On day 4, itraconazole increased the MedChem Express HY-17514
      Microbiology & Virology TargetMol T1011
      SMO antagonist (IC50 = 690 nM); acts at different binding site to cyclopamine (Cat. No. 1623). Also cytochrome p450 inhibitor (IC50 = 16-26 nM). Inhibits cell cycle at G1 phase in vitro and blocks angiogenesis in vivo (IC50 = 160 nM). Antifungal. Tocris Bioscience 5981
      SMO antagonist; acts at different binding site to cyclopamine (Cat No. 1623) Tocris Bioscience 5981
      Smoothened Receptors Tocris Bioscience 5981

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.4±0.1 g/cm3
Boiling Point: 850.0±75.0 °C at 760 mmHg
Vapour Pressure: 0.0±3.2 mmHg at 25°C
Enthalpy of Vaporization: 123.5±3.0 kJ/mol
Flash Point: 467.9±37.1 °C
Index of Refraction: 1.678
Molar Refractivity: 189.3±0.5 cm3
#H bond acceptors: 12
#H bond donors: 0
#Freely Rotating Bonds: 11
#Rule of 5 Violations: 2
ACD/LogP: 4.35
ACD/LogD (pH 5.5): 3.90
ACD/BCF (pH 5.5): 291.92
ACD/KOC (pH 5.5): 971.97
ACD/LogD (pH 7.4): 4.96
ACD/BCF (pH 7.4): 3338.91
ACD/KOC (pH 7.4): 11117.17
Polar Surface Area: 101 Å2
Polarizability: 75.1±0.5 10-24cm3
Surface Tension: 55.9±7.0 dyne/cm
Molar Volume: 502.0±7.0 cm3

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